1-[6-(9H-Carbazol-9-yl)hex-yl]-2-phenyl-1H-benzimidazole.

The mol-ecule of the title compound, C(31)H(29)N(3), contains a hexyl chain, a coordination unit (benzimidazole) and a functional group (carbazole). The benzimidazole ring is not coplanar with either the phenyl ring or the carbazole system, making dihedral angles of 43.26 (3) and 39.03 (2)°, respectively. The dihedral angle between the phenyl ring and the carbazole system is 24.42 (3)°. The hexyl C(β) atom (with respect to benzimidazole) deviates by 1.124 (2) Å from the benzimidazole plane, although the C(α) atom lies in the plane. The hexyl C(β) atom (with respect to carbazole) deviates by 1.315 (1) Å from the carbazole plane, although the C(α) atom lies in the plane. The crystal structure is stabilized by inter-molecular C-H⋯π inter-actions.

Related literature

For applications of benzimidazole-containing compounds as human cytomegalovirus inhibitors and anthelmintic agents, see: Spasov et al. (1999 ▶); Zhu et al. (2000 ▶). Benzimidazole derivatives can act as ligands to transition metals for modeling biological systems, see: Bouwman et al. (1990 ▶) and for organic light-emitting devices (OLEDs), see: Huang et al. (2004 ▶); Si et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C31H29N3

M = 443.57

Monoclinic,

a = 8.6623 (6) Å

b = 31.582 (2) Å

c = 8.9187 (6) Å

β = 96.3120 (10)°

V = 2425.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 293 K

0.43 × 0.18 × 0.12 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.970, T max = 0.991

13496 measured reflections

4757 independent reflections

3374 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.119

S = 1.01

4757 reflections

307 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809046820/jh2111sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809046820/jh2111Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C31H29N3	F(000) = 944
Mr = 443.57	Dx = 1.215 Mg m−3
Monoclinic, P21/c	Melting point = 403–405 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.6623 (6) Å	Cell parameters from 3325 reflections
b = 31.582 (2) Å	θ = 2.4–24.3°
c = 8.9187 (6) Å	µ = 0.07 mm−1
β = 96.312 (1)°	T = 293 K
V = 2425.1 (3) Å3	Tabular, yellow
Z = 4	0.43 × 0.18 × 0.12 mm

Bruker SMART APEX CCD area-detector diffractometer	4757 independent reflections
Radiation source: fine-focus sealed tube	3374 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 26.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.970, Tmax = 0.991	k = −18→38
13496 measured reflections	l = −10→11

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0541P)2 + 0.1994P] where P = (Fo2 + 2Fc2)/3
4757 reflections	(Δ/σ)max < 0.001
307 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	−0.02475 (16)	0.43714 (5)	0.59089 (17)	0.0523 (4)
C2	−0.12646 (18)	0.40495 (6)	0.5389 (2)	0.0653 (4)
H2	−0.1038	0.3866	0.4627	0.078*
C3	−0.2618 (2)	0.40148 (7)	0.6050 (2)	0.0791 (5)
H3	−0.3313	0.3800	0.5737	0.095*
C4	−0.2981 (2)	0.42893 (7)	0.7167 (2)	0.0820 (6)
H4	−0.3912	0.4256	0.7583	0.098*
C5	−0.19874 (19)	0.46114 (6)	0.76719 (19)	0.0693 (5)
H5	−0.2245	0.4798	0.8412	0.083*
C6	−0.05852 (17)	0.46530 (5)	0.70515 (16)	0.0539 (4)
C7	0.07318 (18)	0.49316 (5)	0.73388 (16)	0.0543 (4)
C8	0.1095 (2)	0.52700 (6)	0.83139 (19)	0.0702 (5)
H8	0.0393	0.5360	0.8964	0.084*
C9	0.2502 (3)	0.54688 (7)	0.8303 (2)	0.0851 (6)
H9	0.2746	0.5697	0.8945	0.102*
C10	0.3566 (2)	0.53354 (6)	0.7351 (2)	0.0851 (6)
H10	0.4517	0.5473	0.7376	0.102*
C11	0.3241 (2)	0.50022 (6)	0.6364 (2)	0.0682 (5)
H11	0.3956	0.4913	0.5726	0.082*
C12	0.18125 (17)	0.48054 (5)	0.63596 (16)	0.0524 (4)
C13	0.19565 (18)	0.42690 (5)	0.42926 (17)	0.0581 (4)
H13A	0.2482	0.4483	0.3758	0.070*
H13B	0.1172	0.4139	0.3578	0.070*
C14	0.31251 (17)	0.39346 (5)	0.48825 (18)	0.0567 (4)
H14A	0.3657	0.3830	0.4055	0.068*
H14B	0.3895	0.4062	0.5617	0.068*
C15	0.23723 (17)	0.35671 (5)	0.56068 (18)	0.0548 (4)
H15A	0.1568	0.3451	0.4879	0.066*
H15B	0.1870	0.3674	0.6450	0.066*
C16	0.34575 (17)	0.32109 (5)	0.61709 (19)	0.0592 (4)
H16A	0.4312	0.3327	0.6839	0.071*
H16B	0.3888	0.3083	0.5319	0.071*
C17	0.26530 (18)	0.28701 (5)	0.70071 (17)	0.0571 (4)
H17A	0.3424	0.2672	0.7459	0.069*
H17B	0.2156	0.3000	0.7814	0.069*
C18	0.14417 (17)	0.26304 (5)	0.59738 (16)	0.0545 (4)
H18A	0.0780	0.2833	0.5395	0.065*
H18B	0.1966	0.2464	0.5268	0.065*
C19	−0.07789 (17)	0.24836 (5)	0.74837 (16)	0.0563 (4)
C20	−0.1313 (2)	0.28859 (6)	0.7791 (2)	0.0696 (5)
H20	−0.0829	0.3129	0.7484	0.084*
C21	−0.2595 (2)	0.29058 (8)	0.8573 (2)	0.0839 (6)
H21	−0.2985	0.3170	0.8801	0.101*
C22	−0.3322 (2)	0.25458 (9)	0.9029 (2)	0.0886 (6)
H22	−0.4174	0.2573	0.9572	0.106*
C23	−0.2812 (2)	0.21486 (8)	0.8698 (2)	0.0789 (5)
H23	−0.3316	0.1908	0.8994	0.095*
C24	−0.15163 (18)	0.21176 (6)	0.79052 (18)	0.0615 (4)
C25	0.04203 (18)	0.19127 (5)	0.67728 (17)	0.0557 (4)
C26	0.1556 (2)	0.16414 (5)	0.61244 (17)	0.0583 (4)
C27	0.1020 (2)	0.12817 (6)	0.5325 (2)	0.0752 (5)
H27	−0.0039	0.1225	0.5171	0.090*
C28	0.2057 (3)	0.10106 (6)	0.4763 (2)	0.0905 (6)
H28	0.1690	0.0772	0.4227	0.109*
C29	0.3625 (3)	0.10872 (7)	0.4982 (2)	0.0906 (6)
H29	0.4314	0.0900	0.4601	0.109*
C30	0.4175 (2)	0.14419 (6)	0.5768 (2)	0.0822 (6)
H30	0.5236	0.1496	0.5915	0.099*
C31	0.3140 (2)	0.17165 (5)	0.63358 (19)	0.0675 (5)
H31	0.3513	0.1955	0.6868	0.081*
N1	0.12011 (13)	0.44707 (4)	0.54812 (14)	0.0530 (3)
N2	0.04699 (14)	0.23494 (4)	0.67667 (13)	0.0532 (3)
N3	−0.07470 (16)	0.17632 (4)	0.74442 (15)	0.0653 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0462 (8)	0.0539 (9)	0.0569 (9)	0.0074 (7)	0.0055 (7)	0.0089 (7)
C2	0.0521 (9)	0.0678 (11)	0.0752 (11)	0.0046 (8)	0.0042 (8)	−0.0036 (9)
C3	0.0518 (10)	0.0915 (14)	0.0937 (14)	−0.0075 (10)	0.0067 (10)	−0.0035 (12)
C4	0.0504 (10)	0.1153 (17)	0.0822 (13)	−0.0060 (11)	0.0164 (9)	0.0027 (12)
C5	0.0578 (10)	0.0922 (14)	0.0591 (10)	0.0098 (10)	0.0113 (8)	0.0009 (9)
C6	0.0499 (8)	0.0616 (10)	0.0502 (8)	0.0108 (8)	0.0051 (7)	0.0091 (7)
C7	0.0607 (9)	0.0530 (9)	0.0490 (8)	0.0085 (8)	0.0055 (7)	0.0067 (7)
C8	0.0806 (12)	0.0711 (12)	0.0597 (10)	0.0051 (10)	0.0111 (9)	−0.0055 (9)
C9	0.1004 (15)	0.0742 (13)	0.0810 (13)	−0.0167 (12)	0.0114 (11)	−0.0152 (10)
C10	0.0847 (13)	0.0765 (13)	0.0953 (14)	−0.0245 (11)	0.0153 (11)	−0.0006 (11)
C11	0.0692 (11)	0.0612 (11)	0.0774 (11)	−0.0072 (9)	0.0217 (9)	0.0048 (9)
C12	0.0571 (9)	0.0460 (9)	0.0549 (9)	0.0036 (7)	0.0096 (7)	0.0095 (7)
C13	0.0614 (9)	0.0559 (9)	0.0593 (9)	0.0059 (8)	0.0173 (7)	0.0036 (8)
C14	0.0529 (9)	0.0534 (9)	0.0657 (10)	0.0018 (7)	0.0155 (7)	−0.0051 (8)
C15	0.0470 (8)	0.0543 (9)	0.0633 (9)	0.0027 (7)	0.0069 (7)	0.0011 (8)
C16	0.0483 (9)	0.0563 (9)	0.0718 (10)	−0.0002 (7)	0.0020 (7)	−0.0010 (8)
C17	0.0556 (9)	0.0556 (9)	0.0570 (9)	0.0007 (8)	−0.0072 (7)	0.0042 (8)
C18	0.0614 (9)	0.0514 (9)	0.0492 (8)	−0.0038 (8)	−0.0008 (7)	0.0047 (7)
C19	0.0494 (9)	0.0675 (10)	0.0495 (8)	0.0016 (8)	−0.0055 (7)	0.0027 (8)
C20	0.0620 (11)	0.0741 (12)	0.0698 (11)	0.0063 (9)	−0.0058 (9)	−0.0030 (9)
C21	0.0653 (12)	0.1049 (17)	0.0790 (13)	0.0191 (12)	−0.0024 (10)	−0.0109 (12)
C22	0.0565 (11)	0.132 (2)	0.0766 (13)	0.0119 (13)	0.0043 (9)	0.0004 (13)
C23	0.0577 (11)	0.1061 (16)	0.0713 (11)	−0.0047 (11)	0.0005 (9)	0.0150 (11)
C24	0.0500 (9)	0.0769 (12)	0.0552 (9)	−0.0013 (9)	−0.0045 (7)	0.0091 (8)
C25	0.0596 (9)	0.0544 (9)	0.0509 (8)	−0.0056 (8)	−0.0028 (7)	0.0077 (7)
C26	0.0719 (11)	0.0510 (9)	0.0514 (9)	−0.0028 (8)	0.0036 (8)	0.0098 (7)
C27	0.0954 (13)	0.0573 (11)	0.0721 (11)	−0.0074 (10)	0.0051 (10)	0.0008 (9)
C28	0.130 (2)	0.0652 (13)	0.0764 (13)	0.0002 (14)	0.0136 (13)	−0.0099 (10)
C29	0.1219 (19)	0.0758 (14)	0.0791 (13)	0.0205 (14)	0.0334 (13)	0.0018 (11)
C30	0.0835 (13)	0.0815 (14)	0.0845 (13)	0.0088 (11)	0.0221 (11)	0.0086 (11)
C31	0.0760 (12)	0.0589 (10)	0.0680 (10)	0.0024 (9)	0.0101 (9)	0.0019 (8)
N1	0.0529 (7)	0.0477 (7)	0.0601 (7)	0.0043 (6)	0.0135 (6)	0.0019 (6)
N2	0.0552 (7)	0.0522 (8)	0.0506 (7)	−0.0037 (6)	−0.0017 (6)	0.0033 (6)
N3	0.0630 (8)	0.0658 (9)	0.0659 (8)	−0.0074 (7)	0.0024 (7)	0.0131 (7)

C1—N1	1.3870 (18)	C16—H16A	0.9700
C1—C2	1.391 (2)	C16—H16B	0.9700
C1—C6	1.407 (2)	C17—C18	1.520 (2)
C2—C3	1.373 (2)	C17—H17A	0.9700
C2—H2	0.9300	C17—H17B	0.9700
C3—C4	1.382 (3)	C18—N2	1.4585 (18)
C3—H3	0.9300	C18—H18A	0.9700
C4—C5	1.376 (3)	C18—H18B	0.9700
C4—H4	0.9300	C19—N2	1.3823 (19)
C5—C6	1.395 (2)	C19—C20	1.390 (2)
C5—H5	0.9300	C19—C24	1.392 (2)
C6—C7	1.441 (2)	C20—C21	1.377 (3)
C7—C8	1.392 (2)	C20—H20	0.9300
C7—C12	1.406 (2)	C21—C22	1.383 (3)
C8—C9	1.372 (3)	C21—H21	0.9300
C8—H8	0.9300	C22—C23	1.373 (3)
C9—C10	1.386 (3)	C22—H22	0.9300
C9—H9	0.9300	C23—C24	1.395 (2)
C10—C11	1.380 (3)	C23—H23	0.9300
C10—H10	0.9300	C24—N3	1.388 (2)
C11—C12	1.384 (2)	C25—N3	1.3181 (19)
C11—H11	0.9300	C25—N2	1.3799 (19)
C12—N1	1.3858 (19)	C25—C26	1.470 (2)
C13—N1	1.4527 (18)	C26—C31	1.384 (2)
C13—C14	1.517 (2)	C26—C27	1.393 (2)
C13—H13A	0.9700	C27—C28	1.375 (3)
C13—H13B	0.9700	C27—H27	0.9300
C14—C15	1.511 (2)	C28—C29	1.372 (3)
C14—H14A	0.9700	C28—H28	0.9300
C14—H14B	0.9700	C29—C30	1.378 (3)
C15—C16	1.516 (2)	C29—H29	0.9300
C15—H15A	0.9700	C30—C31	1.383 (2)
C15—H15B	0.9700	C30—H30	0.9300
C16—C17	1.521 (2)	C31—H31	0.9300
N1—C1—C2	129.25 (14)	H16A—C16—H16B	107.8
N1—C1—C6	108.82 (13)	C18—C17—C16	112.21 (12)
C2—C1—C6	121.92 (14)	C18—C17—H17A	109.2
C3—C2—C1	117.02 (17)	C16—C17—H17A	109.2
C3—C2—H2	121.5	C18—C17—H17B	109.2
C1—C2—H2	121.5	C16—C17—H17B	109.2
C2—C3—C4	122.15 (18)	H17A—C17—H17B	107.9
C2—C3—H3	118.9	N2—C18—C17	113.94 (12)
C4—C3—H3	118.9	N2—C18—H18A	108.8
C5—C4—C3	121.04 (16)	C17—C18—H18A	108.8
C5—C4—H4	119.5	N2—C18—H18B	108.8
C3—C4—H4	119.5	C17—C18—H18B	108.8
C4—C5—C6	118.71 (16)	H18A—C18—H18B	107.7
C4—C5—H5	120.6	N2—C19—C20	131.73 (16)
C6—C5—H5	120.6	N2—C19—C24	106.03 (14)
C5—C6—C1	119.14 (15)	C20—C19—C24	122.25 (16)
C5—C6—C7	133.92 (15)	C21—C20—C19	116.48 (19)
C1—C6—C7	106.93 (12)	C21—C20—H20	121.8
C8—C7—C12	119.05 (15)	C19—C20—H20	121.8
C8—C7—C6	134.42 (15)	C20—C21—C22	122.1 (2)
C12—C7—C6	106.53 (13)	C20—C21—H21	119.0
C9—C8—C7	119.13 (17)	C22—C21—H21	119.0
C9—C8—H8	120.4	C23—C22—C21	121.35 (19)
C7—C8—H8	120.4	C23—C22—H22	119.3
C8—C9—C10	121.08 (18)	C21—C22—H22	119.3
C8—C9—H9	119.5	C22—C23—C24	118.0 (2)
C10—C9—H9	119.5	C22—C23—H23	121.0
C11—C10—C9	121.31 (18)	C24—C23—H23	121.0
C11—C10—H10	119.3	N3—C24—C19	109.88 (14)
C9—C10—H10	119.3	N3—C24—C23	130.28 (17)
C10—C11—C12	117.63 (17)	C19—C24—C23	119.83 (18)
C10—C11—H11	121.2	N3—C25—N2	112.69 (14)
C12—C11—H11	121.2	N3—C25—C26	123.34 (15)
C11—C12—N1	129.06 (14)	N2—C25—C26	123.96 (13)
C11—C12—C7	121.78 (15)	C31—C26—C27	118.61 (17)
N1—C12—C7	109.16 (13)	C31—C26—C25	122.84 (15)
N1—C13—C14	112.91 (12)	C27—C26—C25	118.47 (16)
N1—C13—H13A	109.0	C28—C27—C26	119.99 (19)
C14—C13—H13A	109.0	C28—C27—H27	120.0
N1—C13—H13B	109.0	C26—C27—H27	120.0
C14—C13—H13B	109.0	C29—C28—C27	121.0 (2)
H13A—C13—H13B	107.8	C29—C28—H28	119.5
C15—C14—C13	112.35 (12)	C27—C28—H28	119.5
C15—C14—H14A	109.1	C28—C29—C30	119.8 (2)
C13—C14—H14A	109.1	C28—C29—H29	120.1
C15—C14—H14B	109.1	C30—C29—H29	120.1
C13—C14—H14B	109.1	C29—C30—C31	119.6 (2)
H14A—C14—H14B	107.9	C29—C30—H30	120.2
C14—C15—C16	115.52 (12)	C31—C30—H30	120.2
C14—C15—H15A	108.4	C30—C31—C26	121.00 (18)
C16—C15—H15A	108.4	C30—C31—H31	119.5
C14—C15—H15B	108.4	C26—C31—H31	119.5
C16—C15—H15B	108.4	C12—N1—C1	108.55 (12)
H15A—C15—H15B	107.5	C12—N1—C13	124.91 (12)
C15—C16—C17	112.76 (12)	C1—N1—C13	126.53 (13)
C15—C16—H16A	109.0	C25—N2—C19	106.15 (13)
C17—C16—H16A	109.0	C25—N2—C18	129.05 (13)
C15—C16—H16B	109.0	C19—N2—C18	124.10 (13)
C17—C16—H16B	109.0	C25—N3—C24	105.24 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C28—H28···Cg1	0.93	2.78	3.665 (2)	159
C18—H18A···Cg2	0.97	2.87	3.596 (3)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C28—H28⋯Cg1	0.93	2.78	3.665 (2)	159
C18—H18A⋯Cg2	0.97	2.87	3.596 (3)	133

Cg1 and Cg2 are the centroids of the 13-atom carbazole ring and the C19/C24/C25/N2/N3 imidazole ring, respectively.